


Pick Me Up

by relic_amaranth



Category: Supernatural
Genre: Bad Pick-Up Lines, Double Penetration, Explicit Language, Explicit Sexual Content, F/M, Flirting, Friends With Benefits, Innuendo, M/M, Multi, Oral Sex, PWP, Reader-Insert, Smut, Some Fluff, Threesome - F/M/M
Language: English
Status: Completed
Published: 2018-02-12
Updated: 2018-06-20
Packaged: 2019-03-17 04:24:25
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 2
Words: 4,311
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/13651374
Author URL: https://archiveofourown.org/users/relic_amaranth/pseuds/relic_amaranth
Summary: You set out to give Castiel an experience and he and Dean end up turning that back on you. Terrible, awful pick-up lines– who knew they worked so well?Chapter 2: Now with actual sex.





	1. Chapter 1

**Author's Note:**

> I have a thing for bad pick-up lines. ‘A thing’ meaning ‘I love them too much and I’m not sorry for it.’ This…well, it is what it is. The smut wasn’t working (I’m baaaad) so I cut it out, but I really like this half at least so I’m posting it. Enjoy! [Cross-posted to Tumblr]

 

The bar is busy but the side you’re on is opposite the pool tables and darts and is much quieter by comparison. Surprisingly so, but maybe that’s Gabriel’s doing. It’s also fairly close to the counter but the harried bartenders don’t have to worry about your group, what with an archangel that finds delight in trying to get his humans hilariously drunk. You’re pretty sure Dean would balk at the possessive title but Gabriel– and Castiel– have said it offhandedly on a couple of occasions and you’re okay with owning it. Dean’s always been fairly decent at denial but you’re sober enough to keep it to yourself.

Just barely.

Sam is smiling and laughing at something Gabriel says and it fuels your heart to see all your friends so happy and relaxed. This is pretty much what Heaven should be, in your opinion, but you’re _definitely_ going to keep that one to yourself. You lick your lips of alcohol and watch as Dean leans in closer to Castiel to murmur something that makes the angel smile. In this group it’s easy to feel like a fifth wheel and maybe you get a little lonely sometimes, but you’d rather have them than not.

Gabriel and Sam are great to be around and so are Dean and Castiel, but the latter couple can also frustrate the fuck out of you. A slim alleyway behind stores, a dark corner of a skuzzy bar, the backseat of the Impala (double unfair since that’s where _you_ have to sit); they’re practically exhibitionists and considering how stupidly beautiful they both are it’s caused some…issues, if you’re going to be kind about it.

Cas turns to you, looking as innocent as ever, and you slowly smile, thinking of how he’s missed out on a typical terrible bar experience by virtue of already having found his partner. Such a shame. You really should fix that.

Cas blinks and has the good sense to look worried, but Dean just raises an eyebrow and looks between you two…and sits back. You shoot him a quick wink, and lean in closer to your target. “Hey Cas,” you say, grinning with abandon. You’re not trying to actually seduce him, so sexy gets tossed in the bin in favor of drunken delight. “Do you know how much a polar bear weighs?”

He frowns in thought. “The average mass of–”

“Enough to break the ice,” you say and add a stupidly exaggerated wink.

Sam chokes on his beer and Gabriel laughs as he pats his boyfriend’s back. Dean shakes his head but looks amused. That’s all the encouragement you need. Well, that’s a lie– Castiel is too freaking cute when he’s confused and _that’s_ all the encouragement you need. The others are a bonus.

“You know what’s on the menu?” you ask. He grabs the actual menu and you put your hand on top of it. “Me ‘n you.”

His face crinkles. “We are? How is–”

“Do you believe in love at first sight, or should I walk by again?”

“I do not believe any cupid would interfere with Dean and I like that.”

“Cas, if you were a fruit, you’d be a _fine_ -apple.”

“That doesn’t exist.”

“And if you were a vegetable, you’d be a _cute-_ cumber.”

“That also does not exist.”

Sam already has his face in his arms on the table and Gabriel collapses, giggling madly, into the same position.

“Sweetheart, your eyes are as blue as the ocean and I’m lost at sea,” you say and flutter your eyelashes.

The Winchesters have a common problem with inhaling their beer, apparently, because Dean chokes on a laugh and then on his drink. Castiel is so focused he doesn’t take his eyes off you– just touches Dean’s forehead to clear his airways. He waits a moment, bending his fingers, (and that’s a mental image you’re going to keep on cold nights; his hands are practically obscene all on their own), fidgeting. He reaches out to you, but you grab his hand and hold his palm to your cheek. It’s large and warm. “Is it bright in here, or is that just your halo?”

Gabriel might be laughing so hard he’s almost crying, but it’s hard to tell with his face hidden. Sam is slightly red but he’s watching with a restrained grin that you want to break. You lean in and Castiel obviously has to stop himself from leaning back. It’s actually kind of cute how concerned he is for you. “Baby I must be in Heaven ‘cause I’m looking at an angel.”

“(Y/n) you _know_ I’m an angel,” Castiel says, his tone very much ‘I should not have to explain this to you’ and _that_ makes Dean break into a fit, which in turn breaks you, and the both of you are laughing now. Castiel looks between you two and his brow furrows into a glare while his mouth twists into a pout.

Oops.

Nah, not really.

The scowl isn’t a serious one (you’ve learned to tell the difference), and the angel is slightly mollified by Dean pulling him in with a heavy arm and placing a firm kiss on his cheek. It’s cute. It makes your heart ache a little, but Castiel’s smile at Dean repairs it just as quick. They’re good together and, if you’re going to be honest, they’ve given you enough solo material for a lifetime. You’ll take what you can get.

“Thanks for being a good sport Cas,” you say and hop up to give him (and Dean) a friendly kiss to the temple. “I’ll be right back. Gotta take care of business.”

“If that’s all it takes then do I have some lines for you,” Gabriel says, waggling his eyebrows. You smack him in the shoulder, heedless of strength since you know he can take it, and your laughter matches theirs as you walk away.

 

When you get back, the table is calm again and Cas looks much more comfortable. In fact…

He clears his throat and looks at you, excitement telegraphed in his eyes. By the way Gabriel is practically bouncing and Dean is smug, and Sam is ‘casually’ paying full attention, you know this is going to be good, and you take a swig of your drink to hide your smile.

“Do you work for UPS? Because I’m fairly certain I saw you checking out my package.”

That…is so much smoother than you would have expected it to be, coming from Cas’s lips, and you’re left blinking. He looks proud of himself. He should. A line like that shouldn’t sound that good, even with that voice.

Dean leans in, making eye contact with you. “If I had a garden I’d put my two lips by your two lips,” he says, glancing at where your lap is under the table and winking.

Hmm. This is interesting. Dean isn’t laying it on thick like he does when the two of you play-flirt; it’s as serious as ridiculous pick-up lines can be and for a panicked moment you wonder if that’s on purpose to make a really strong statement, and you’re about to get the rug pulled out so hard it hurts.

But. Dean and Cas are, above all, your friends, and you think, fuck it– might as well see where this goes. So you look between them, dialing back the hilarity. “We should get breakfast together,” you say, making sure to include them both with quick glances. “Should I call, or just nudge you?”

“I may not get your virginity but can I have the box it came in?” Dean asks, and Gabriel falls on Sam, laughing.

“Kissing is the language of love,” you tell him and wink at Cas. “Wanna have a conversation?”

“This is going to get gross,” Sam chuckles, throws a few bills on the table, and drags his laughing lover out. He must have missed the ‘two lips’ look if that’s his exit line but you think, _I sure hope so_ , in response.

Dean, of course, rises to the challenge. “The word for tonight is legs.” Even the way his smile grows seems filthy and your heart picks up with the thought, the hope, that this is actually serious. “Wanna spread the word?”

You bite your lip and try to think of a good line to up the ante even more. Cas tilts his head to one side and smirks. You try not to show how much that smirk, how much Dean’s smile, gets to you. Blue eyes look up at you through dark, full lashes. “I have a tongue like an anteater. Would you like to go to the zoo?” he says, lowly, in a way that makes you bite your tongue to keep from begging _please_.

You bite a little too hard and giggle to cover it up. “Holy shit. You win.” You re-center yourself. This is fun, these are friends, this is…nothing.

But they don’t stop looking at you like _that_. Even when you compose yourself and study them– Cas especially. He glances at Dean, who smiles and nods, and Cas slides his hand across the table to cover yours. “I would say so, if I didn’t find it agreeable,” he says, serious now.

That makes you skip a breath. They’re looking at you with a confidence that devours and you feel just as hungry. This is fun, but this is also _something_.

You bite your bottom lip to contain a stupid smile. “Then let’s go.” 


	2. Chapter 2

**Summary for the Chapter:**

> Dean and Cas bring you along for an intimate look into their relationship, but you're definitely not just an observer.

**Notes for the Chapter:**

> Warnings: PWP. Threesome. M/M/F. Or rather M/F/M I guess. DP. Blunt language when it comes to fucking (come as verb and cum as product, cunt, cock, etc).
> 
> A/N: I had no intention of posting this. A few days ago there were just snippets of unfinished smut, like most NC17 stuff I write, then suddenly it got…a beginning, middle, and end. And since getting back into writing fanfic is trying new stuff, I thought ‘what the hell’, so here I am, posting it. If it bores you: sorry! If you’re into it: cool! I do hope you enjoy it, but smut/erotica/whatever you want to call it can be divisive and I know not everybody is into the type of vocabulary I chose to use, so please note the warning above.

 

 

Somehow you all make it back to the motel room without getting indecent. ‘Somehow’ being the guy with wings pressing up behind you, grabbing Dean so that he’s pressed just as tight against your front, suddenly flying you into the dark, sort-of-cold room with only a slight stumble.

“Damn it Cas,” Dean groans and you let out a nearly hysterical laugh because you are seriously going to fuck this hot-as-hell hunter and his not-ironically-angelic boyfriend.

They’re pressed even tighter to you as they kiss over your shoulder and you can hear it but you can’t see it. It’s maddening. “We need a light,” you say. “No way am I missing this.”

They pull apart, Dean chuckling lowly as his hands run down your sides. “You ain’t missing anything, sweetheart,” he says and grips onto your t-shirt and pulls it over your head. But a light does come on and you blink a bit to adjust. It’s a low light but you look behind to see Cas glancing curiously over you.

“You okay, angel?” you ask and turn in Dean’s arms. Castiel seems to take you in, and his intense blue eyes focus on your chest. A smile grows on your face. “Thanks, but they’re not _that_ great.”

Dean chuckles in your ear and his hands work magic to unhook and drop your bra onto the floor in milliseconds. “Cas has never been with a woman before,” Dean says, his breath hitching with excitement. You can hear him lick his lips and you turn your head to taste them for yourself, beckoning Cas closer with a wave of your hand.

He stumbles into orbit and, what the hell; you grab his tie and pull him in as you turn away from Dean, so rough that his mouth almost knocks into yours. Cas is startled by the kiss, but Dean has taught him well, and he finds his bearings quickly enough, latching onto you with intense focus. Dean is soft and tender whereas Cas is soft, yes, but he’s so forceful it’s like he’s trying to drink you up. You moan into Cas as Dean brings the angel’s hands up to hold your breasts.

Cas calms then and pulls back, seemingly mystified. “They’re so soft,” he murmurs and you let out a little giggle. You’re about to give him some pointers when he suddenly pinches your nipple and you yelp. He smiles mischievously and looks at Dean. “She makes the same sound you do.”

“I do not sound like that!” Dean protests and you laugh. They’re so cute together but even as they kiss each other, they keep touching you. Rough, calloused hands run gently over your breasts, your stomach, down to slip fingers under the top of your jeans. You arch back into Dean and try to control your breathing.

“Hey, hey,” you say and as they part from each other you turn in their hold again, taking Cas’s hands back up to your breasts where he massages them, palms them, feels them over. You grab Dean’s collar, trying not to get distracted by his plump, wet lips, and tug on the clothing. “Why am I the only one with a shirt off?”

Dean grins like the cocky bastard he is. “Yeah, we’re a bit overdressed. Luckily Cas has the best party trick to take care of that.”

Cas, his head on your shoulder, chuckles darkly at that and suddenly you’re wondering where your pants are, but when you realize you are ensconced by skin and skin, you stop wondering about much at all. Cas’s cock is up against your back and Dean starts rubbing his against your front. You lean your head back and lick your lips and Dean kisses your neck, sucking hard at spots like he’s trying to mark you. “Come on Cas,” he says and starts moving you all backwards. “I’m gonna teach you the best thing you can do with a woman.”

You expect to be giving head at any moment now, which, given what you feel at your back, you honestly don’t really mind. But you go a little cross-eyed when Dean’s magic fingers start rubbing at your clit and you rock against his hand, only to try and stop yourself from coming before you even get to the bed.

That’s when you notice Dean and Cas are whispering to each other, but you tune in too late when they stop talking and exchange a sweet kiss. “Hey,” you say, a smile ruining the warning tone you’re going for. “What’s with the secrets?”

“Trust me baby, you’re gonna like this,” Dean says, but you lose the warmth at your back as Cas moves away. You turn your head to see him go lie on his back on the bed, head on the pillow and waiting. After a moment he shifts down, a little further away from the headboard.

“Go on, sweetheart.” Dean nips at your ear. “Go sit on his face. I’ll tell him what to do.”

A thrill curls up in your gut and you swallow hard. You control yourself, carefully maneuvering your knees on either side of Castiel’s head. The sight of him, blue eyes looking right at you as you settle your vagina right in front of his mouth, does something to you, making your skin prickle all over.

Then he licks up, tentatively, tongue slipping past your lips and grazing your clit and you can’t hold back the cry that escapes you. Cas then grabs your thighs and brings you closer, kissing your cunt and you vacillate between wanting to push down and wanting to pull back from the intense stimulation.

“Use your tongue to fuck into her, Cas,” Dean says and _oh_ Cas _does_.

“Shit that’s hot,” Dean says, groaning as the bed shifts. “Cas is so fucking hard, baby girl. I think he likes you.”

The phrase is said flippantly but you really, _really_ like him too. You really, really like them both; especially right now. But as you glance back over your shoulder to say something to Dean, you see him licking his lips and looking at Cas’s stiff cock. “Wait,” you gasp and Cas pulls back obediently. You can just imagine him, his lips red and wet with _you_ , so you don’t look down, but he makes a disgruntled sound and you smile. “Don’t worry Cas, I’m not going anywhere,” you say and turn your body carefully so you don’t knock his head with your knees. You settle back in over his face, gripping the headboard with your arms outstretched. “I just wanna watch Dean suck you off.”

Cas is back, tasting you with maddening little licks and kisses, and his moan reverberates through your cunt. You moan too and Dean chuckles, kissing up Castiel’s shaft. Dean makes eye contact with you, still teasing his boyfriend. “You want a show, sweetheart?”

“Pretty please?” you ask, accidentally slurring a bit so it comes out more like a purr.

“No need to beg.” Dean winks. “Yet.” He gives Cas a strong, quick lick that startles the angel into thrusting his tongue deep into you. You yell in surprise and pleasure and Dean shakes with suppressed laughter. “He liked that, did he?”

Cas seems to get how nice that was and as Dean starts licking and touching him, Cas returns the favor onto you with enthusiasm. You guide with nonverbal cues (and some startled verbal ones), rocking and moaning as Cas slowly builds you up while Dean, fucking perfect man he is, deepthroats Cas like a fucking champ. “Your angel’s a real quick study,” you pant as Cas holds your hips in place and smoothly, torturously, fucks you with his tongue.

Dean pops off Cas’s rock hard, leaking cock and smirks at you. “Damn straight.”

You grin, because neither of those words fit the situation. Still. You reach down and squeeze Castiel’s hands and say, as low as your voice can go, “I love what you’re doing, sweetie, but I don’t suppose I could watch you repay Dean for the favor?”

Dean shudders and Cas chuckles– right before he slides his tongue and mouth up to your clit and with one quick nip and suck you’re coming so hard you have to blink away stars. Cas isn’t holding you in place so much as he’s just holding you up, and when he extricates himself you almost sink into the pillows.

“Stay,” Cas commands, for whatever reason, and you obey, even though your legs feel so fucking weak. You lick your lips and watch Cas move to sit behind Dean, who…stares at you, like you’re the hottest thing he’s seen.

“We’ll have to show you that some other time.” Cas lightly strokes Dean’s just-as-impressive, just-as- _hard_ , length, almost pulling out the pre-cum. “Dean is more than ready.”

“Fuck, can you blame me?” Dean groans and shuts his eyes. Only for a moment. “That was fucking hot. You’re _dripping_ , baby girl.”

You feel like you’re fire, burning up with no intent to stop, and you wiggle your hips. “How you boys wanna do this?”

Dean brings Cas’s hand up to kiss. “You got a preference, Cas?”

Cas stares at you. You shudder, feeling like he’s stripping deeper into you with his eyes. Apparently, he sort of is, because _you_ have a preference. “She has…quite a nice idea.”

“Hey.” You fake-pout. “You going in my head, sweetie?”

“I couldn’t help it,” he says, blushing and pushing his face into Dean’s shoulder. It’s so freaking cute, you can’t help but smile.

“Well if we’re gonna make a sandwich of me, I’m gonna need a little bit more help,” you say, looking right at Dean. You don’t miss the way his eyes light up, and that dangerous smile sets you all aflutter.

“Oh fuck _yes_ ,” he says. He glances at Cas, and then smirks at you. “Bend over, baby girl. I think Cas deserves a show this time.”

Cas’s eyes flash and you need no more prodding. You turn around, bend over, and push your ass back, feeling quite obscene, in your opinion. It’s a shame you can’t see Cas, but you hear him let out a little groan as Dean kneels next to you. You bite your lip as he works the lube around your rim. “Don’t take too long, sweetheart. There’s only two places I want you to blow your loads, and both of them are in me.”

“Shit. Fucking filthy,” Dean groans against his own pleasure and you let out a pleasured sound of your own as he slips a finger in. “Cas. Condoms.”

You can hear Cas dutifully going to work and Dean doesn’t falter as he loosens you up. Dean slides in another finger, and then one more, and you have to make yourself breathe and relax against pure anticipation.

“Are you ready, sweetheart?” Dean asks and leans next to your ear. “You ready for me and Cas to slide up inside you? Fuck you raw?”

You roll your eyes. “Put up or shut up, Winchester,” you say and look back, between him and Cas. “Choose where you want to be, before I come without you.”

“You wouldn’t,” Dean growls playfully, and flips you around so your back is pressed against his front. He swipes his fingers in your pussy and starts lubing himself up with your body. Cas stares at you hungrily, eyes gleaming in the light like an expectant predator. “Come on, Cas. It’s your first time fucking a cunt.”

You laugh and throw back your head as Dean slowly enters you from behind. “That better be a general noun and not a proper one, or I’ve got some names for you,” you grunt as you sink down on him. Once Dean is settled, Cas, with Dean’s guidance, enters you as well.

“Nah. We’ll save the name calling for some other time,” Dean promises darkly and all you can think is ‘oh fuck _yes_.’

Then they start moving. Well, Dean does, and he and Cas work to find a rhythm. At first it’s strange, feeling them enter and almost exit at the same time, filling you almost uncomfortably, but then they get it. You’re pulled back and forth, Dean and Cas thrusting in to each other’s out, and vice versa, and the heat builds and builds, and it feels like almost no time at all that you start playing with your own clit because you just have to come, _now_. Cas is first, pulsing inside your body and letting out something between a moan and a cry, and the sound sets off Dean as well, so that he jerks and digs his fingers into your hips right on the heels of his boyfriend. A little more rubbing and your own orgasm drags itself out in a rolling wave, your body clenching around the two men going soft inside of you and drawing out some more moans until you’re all wrung out, sitting and panting.

Well, panting in the case of the two humans. Cas’s forehead is pressed into your shoulder, and you tilt your head to give his ruffled, sweaty dark hair a little kiss. “Great job for your first time with a woman. A plus; would fuck again.”

“Thank you.” Cas lifts his head and, to your surprise, presses a soft kiss to your lips. “I quite enjoyed myself as well.”

“Yeah, yeah. Go team,” Dean mumbles sleepily and pulls out of you, as does Cas. “Ugh; what a mess. Cas?”

Cas rolls his eyes but his smile is fond. There’s no fanfare– one moment you’re all filthy on a spotted-wet bed, the next you’re all clean and there’s no condom or mess to be seen anywhere. You don’t even have to go to the bathroom. You’re tired, but as Dean and Cas fall onto the bed, you hesitate and look for your clothes, suddenly feeling like an interloper. “Thanks. I…I should…”

Dean grunts and yanks you down, wrapping one arm around you and pulling you close while he does the same to Cas with the other. “Not gonna kick you out. Now go to sleep.”

Cas is unperturbed and smiles at you across Dean’s chest. You smile back and shut your eyes. You might be an interloper, but they make you feel welcome, and you’re going to enjoy the feeling for all it’s worth. As you drift to sleep, you feel the gentle caress of feathers on your arm, and you go to sleep feeling warm and content.

 

 

The next day you’re packing up your car while the boys get their stuff into their own ride. Dean and Cas each come over to hug you goodbye, and Sam stands awkwardly by the car, like he really doesn’t even want to think about what you just did with his brother and best friend. You can understand it. But only sort of. You’re pretty sure you’ll never stop thinking about it.

“Back to the sausage fest, I guess,” Gabriel sighs heavily and leans against your trunk.

“It’s not like it’s forever,” you say.

“Mm hm.” Gabriel eyes you up and down. “My little bro treat you right?”

You let out a little laugh. “Of course,” you say. “But that’s all you get. I don’t kiss and tell.”

“Right, right,” Gabriel raises his hands defensively but the look he gives you is wicked and you brace yourself. However he leans in and says, “I’m sure they were fine and all…but if you want a real ride, next time give me and Sam a call, okay?”

You stare at him for a moment, wondering if this is a joke, but you glance at Sam and can see the reddening of his cheeks from where you are. He flashes you a smile and then slips into the car, and you look back at Gabriel who is awaiting a response.

“I’ll…definitely consider that,” you say, trying not to get too into the mental image of that. Gabriel winks at you, and just as Dean honks his horn the trickster-angel is suddenly in the backseat next to Sam, yelling at Dean to get a move on already. The Impala roars out of the parking lot and you watch them go until you can’t see them anymore. Those boys are going to be the death of you.

For once in your hunting life, you’re into it.

**Notes for the Chapter:**

> While the ending is not a promise, I wanted to keep my options open if the mood struck me. Never say never is something I’m learning by practicality, apparently.


End file.
